Herbicidal sulfonylureas

ABSTRACT

Substituted N-arylsulfonyl-N&#39;-pyrimidinylureas and N-arylsulfonyl-N&#39;-triazinylureas of the general formula ##STR1## wherein R 1  is a ##STR2## R 2  is hydrogen, halogen, nitro, C 1  -C 3  alkyl, C 1  -C 3  alkoxy or --COOR 9 , 
     R 3  is hydrogen, C 1  -C 3  alkyl or C 1  -C 3  alkoxy, 
     R 4  and R 5  are each independently of the other hydrogen, halogen, C 1  -C 4  alkyl, C 1  -C 4  haloalkyl, C 1  -C 4  alkoxy, C 1  -C 4  haloalkoxy, C 1  -C 4  alkylthio, C 1  -C 4  haloalkylthio, C 2  -C 4  alkoxyalkyl, C 3  -C 6  -cycloalkyl or --NR 10  R 11 , 
     R 6  is hydrogen or C 1  -C 3  alkyl, 
     R 7  is hydrogen or methyl, 
     R 8  is C 4  -C 6  cycloalkanonyl which is unsubstituted or substituted by C 1-C   3  alkyl or halogen; C 3  -C 6  cycloalkyl which is unsubstituted or substituted by one or more identical or different members selected from the group consisting of C 1  -C 3  alkyl, C 1  -C 3  alkoxy, halogen or cyano; or is C 5  -C 6  cycloalkenyl which is unsubstituted or substituted by C 1  14 C 3  alkyl, halogen or cyano, 
     R 9  is C 1  -C 3  alkyl or allyl, 
     R 10  and R 11  are each independently of the other hydrogen or C 1  -C 4  alkyl, 
     n is 0 or 1, 
     X is sulfur or oxygen, and 
     E and Z are each independently of the other nitrogen or the methine bridge, with the proviso that R 8  is only unsubstituted or substituted C 3  -C 6  cycloalkyl if at the same time Z is nitrogen, 
     and the salts of these compounds with amines, alkali metal bases or alkaline earth metal bases, have good pre- and postemergence selective herbicidal and growth regulating properties.

This is a division of application Ser. No. 676,905, filed Nov. 30, 1984,now U.S. Pat. No. 4,643,760.

The present invention relates to novel substitutedN-arylsulfonyl-N'-pyrimidinylureas and N-arylsulfonyl-N'-triazinylureaswith herbicidal and plant growth regulating properties, to thepreparation thereof, to compositions containing them, and to the usethereof for controlling weeds, in particular selectively, in crops ofuseful plants, or for regulating plant growth. The invention furtherrelates to novel substituted arylsulfonylureas obtained asintermediates.

Specifically, the present invention relates to substitutedN-arylsulfonyl-N'-pyrimidinylureas and N-arylsulfonyl-N'-triazinylureasof the formula I ##STR3## wherein R¹ is a ##STR4## R² is hydrogen,halogen, nitro, C₁ -C₃ alkyl, C₁ -C₃ alkoxy or --COOR⁹,

R³ is hydrogen, C₁ -C₃ alkyl or C₁ -C₃ alkoxy,

R⁴ and R⁵ are each independently of the other hydrogen, halogen, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄-alkylthio, C₁ -C₄ haloalkylthio, C₂ -C₄ alkoxyalkyl, C₃ -C₆ cycloalkylor --NR¹⁰ R¹¹,

R⁶ is hydrogen or C₁ -C₃ alkyl,

R⁷ is hydrogen or methyl,

R⁸ is C₄ -C₆ cycloalkanonyl which is unsubstituted or substituted by C₁-C₃ alkyl or halogen; C₃ -C₆ cycloalkyl which is unsubstituted orsubstituted by one or more identical or different members selected fromthe group consisting of C₁ -C₃ alkyl, C₁ -C₃ alkoxy, halogen or cyano;or is C₅ -C₆ cycloalkenyl which is unsubstituted or substituted by C₁-C₃ alkyl, halogen or cyano,

R⁹ is C₁ -C₃ alkyl or allyl,

R¹⁰ and R¹¹ are each independently of the other hydrogen or C₁ -C₄alkyl,

n is 0 or 1,

X is sulfur or oxygen, and

E and Z are each independently of the other nitrogen or the methinebridge, with the proviso that R⁸ is only unsubstituted or substituted C₃-C₆ cycloalkyl if at the same time Z is nitrogen,

and to the salts thereof.

Herbicidally active ureas, triazines and pyrimidines are generallyknown. Recently, sulfonylureas with herbicidal and plant growthregulating properties have been described in European patent applicationNos. 35893, 44211, 44807, 85028 and 94790.

In the definitions of formula I, alkyl denotes straight chain orbranched alkyl, e.g. methyl, ethyl, n-propyl or isopropyl.

Alkoxy denotes methoxy, ethoxy, n-propoxy or isopropoxy, with methoxy,ethoxy or isopropoxy being preferred.

Alkylthio is e.g. methylthio, ethylthio, n-propylthio or isopropylthio,with methylthio and ethylthio being preferred.

Halogen by itself or as moiety of haloalkoxy, haloalkyl or haloalkylthiois fluorine, chlorine and bromine, with fluorine and chlorine beingpreferred.

Alkoxyalkyl is e.g. methoxymethyl, ethoxymethyl, methoxyethyl andethoxyethyl.

The carbocyclic radicals represented by R⁸ within the scope of thisinvention are for example the following radicals: cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, 2-oxocyclobutyl, 3-oxocyclobutyl,2-oxocyclopentyl, 3-oxocyclopentyl, 2-oxocyclohexyl, 3-oxocyclohexyl,4-oxocyclohexyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl,1-cyclohexenyl, 2-cyclohexenyl or 3-cyclohexenyl. Preferred carbocyclicradicals are cycloalkyl radicals, in particular cyclopentyl andcyclohexyl.

The carbocyclic radicals R⁸ can be attached to the oxygen atom direct orthrough a further carbon atom. The direct bond is preferred, i.e. n is0.

Haloalkyl as moiety of another substituent such as haloalkoxy orhaloalkylthio is normally chloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, 2-chloroethyl, 2,2,2,-trifluoroethyl,1,1,2,2-tetrafluoroethyl, pentafluoroethyl,1,1,2-trifluoro-2-chloroethyl, 2,2,2-trifluoro-1,1-dichloroethyl,pentachloroethyl, 3,3,3-trifluoropropyl, 2,3-dichloropropyl,1,1,2,3,3,3-hexafluoropropyl, with fluoromethyl, chloromethyl,difluoromethyl and trifluoromethyl being preferred.

The invention also comprises the salts which the compounds of formula Iare able to form with amines, alkali metal bases and alkaline earthmetal bases, or with quaternary ammonium bases.

Preferred salt-forming alkali metal hydroxides and alkaline earth metalhydroxides are the hydroxides of lithium, sodium, potassium, magnesiumor calcium, most preferably those of sodium or potassium.

Examples of suitable salt-forming amines are primary, secondary andtertiary aliphatic and aromatic amines such as methylamine, ethylamine,propylamine, isopropylamine, the four butylamine isomers, dimethylamine,diethylamine, diethanolamine, dipropylamine, diisopropylamine,di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine,triethylamine, tripropylamine, quinuclidine, pyridine, quinoline andisoquinoline. Preferred amines are ethylamine, propylamine, diethylamineor triethylamine, with isopropylamine, diethanolamine and1,4-diazabicyclo[2.2.2]octane being most preferred.

Examples of quaternary ammonium bases are, in general, the cations ofhaloammonium salts, e.g. the tetramethylammonium cation, thetrimethylbenzylammonium cation, the triethylbenzylammonium cation. Thetetraethylammonium cation, the trimethylethylammonium cation, and alsothe ammonium cation.

Among the compounds of formula I, those compounds are preferred in whichZ is nitrogen and in which either

(a) X is oxygen or

(b) R² is hydrogen or

(c) R³ is hydrogen or

(d) R⁴ and R⁵ are each independently halogen, C₁ -C₃ alkyl, C₁ -C₃alkoxy, di(C₁ -C₃)alkylamino or C₁ -C₃ haloalkoxy, and together containnot more than 4 carbon atoms,

(e) R¹ is --O--R⁸ or

(f) R¹ is --O--CHR⁷ -cyclopropyl.

Among the compounds of the subgroup (e), those compounds areparticularly preferred in which R⁸ is C₃ -C₆ cycloalkyl, in particularcyclopentyl or cyclohexyl.

Further preferred subgroups of compounds of formula I are those in whichX is oxygen, R² and R³ are hydrogen, R⁴ and R⁵ are each independently ofthe other halogen, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, di(C₁ 14 C₃)alkylaminoor C₁ -C₃ haloalkoxy, and together contain not more than 4 carbon atoms,Z is nitrogen and R¹ is a --O--R⁸ radical; and especially those in whichX is oxygen and Z is nitrogen, R² and R³ are hydrogen, R⁴ and R⁵ areeach independently of the other C₁ -C₃ -alkyl, halogen, C₁ -C₃ alkoxy,di(C₁ -C₃)alkylamino or C₁ -C₃ haloalkoxy, and together contain not morethan 4 carbon atoms, and R¹ is C₃ -C₆ -cycloalkoxy, preferablycyclopentyloxy or cyclohexyloxy.

Preferred individual compounds of formula I are:

N-(2-cyclopentyloxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaand

N-(2-cyclopropylmethoxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.

The preparation of the compounds of formula I is generally carried outby the following methods.

A first process for the preparation of the compounds of formula Icomprises reacting a substituted arylsulfonamide of the formula II##STR5## wherein R¹, R² and Z are as defined for formula I, with anN-pyrimidinylcarbamate or N-triazinylcarbamate of the formula III##STR6## wherein E, R³, R⁴, R⁵ and X are as defined for formula I and Ris phenyl, alkyl or substituted phenyl, in the presence of a base.

A second process for obtaining the compounds of formula I comprisesreacting a substituted N-arylsulfonylcarbamate of the formula IV,##STR7## wherein R¹, R², X and Z are as defined for formula I, and R isphenyl, alkyl or substituted phenyl, with an aminopyrimidine oraminotriazine of the formula V ##STR8## wherein E, R³, R⁴ and R⁵ are asdefined for formula I.

Finally, the compounds of formula I may also be obtained by reacting asulfonylisocyanate of the formula VI ##STR9## wherein R¹, R², X and Zare as defined for formula I, with an aminopyrimidine or aminotriazineof the formula V above.

If desired, the ureas of formula I so obtained can be converted intoaddition salts with amines, alkali metal hydroxides or alkaline earthmetal hydroxides, or with quaternary ammonium bases. This conversion iscarried out e.g. by reacting the compounds of formula I with theequimolar amount of a base and removing the solvent by evaporation.

It is convenient to carry out these reactions for obtaining compounds offormula I in aprotic, inert organic solvents. Examples of such solventsare: benzene, toluene, xylene or cyclohexane; chlorinated hydrocarbonssuch as methylene chloride, chloroform, carbon tetrachloride, orchlorobenzene; ethers such as diethyl ether, ethylene glycol dimethylether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane;nitriles such as acetonitrile or propionitrile; amides such asdimethylformamide, diethylformamide or N-methylpyrrolidinone.

The reaction temperatures are preferably in the range from -20° to +120°C. The coupling reactions are normally slightly exothermic and can becarried out at room temperature. To shorten the reaction time or also toinitiate the reaction it is expedient to heat the reaction mixturesbriefly to boiling point. The reaction times can also be shortened byaddition of a few drops of a base or isocyanate as catalyst. Preferredbases are tertiary amines such as trimethylamine, triethylamine,quinuclidine, 1,4-diazabicyclo[2,2,2]octane,1,5-diazabicyclo[4,3,0]-non-5-ene or 1,8-diazabicyclo[5,4,0]undec-7-ene.However, the bases employed may also be inorganic bases, e.g. hydridessuch as sodium hydride or calcium hydride, hydroxides such as sodiumhydroxide or potassium hydroxide, carbonates such as sodium or potassiumcarbonate, or bicarbonates such as potassium or sodium bicarbonate.

The final products of formula I can be isolated by concentrating thereaction mixture and/or removing the solvent by evaporation, and byrecrystallisation or by triturating the solid residue in a solvent inwhich it is poorly soluble, such as an ether, an aromatic hydrocarbon ora chlorinated hydrocarbon.

The intermediates of formula II, IV and VI, in which Z is the methinegroup, are known from published EP application No. 94790 and can beprepared by methods which are known per se.

The intermediates of the formulae II, IV and VI, in which Z is nitrogen,are novel and have been specially developed for the synthesis of thecompounds of formula I. They therefore constitute an object of thepresent invention.

The novel intermediates of the formula II, in which Z is nitrogen, areprepared by procedures which are known per se. Thus, for example, thecompounds of the subformula IIa ##STR10## where R¹ and R² are as definedfor formula II, are obtained by reacting a halopyridinylsulfonamide ofthe formula VII ##STR11## wherein R₂ is as defined for formula I and Halis halogen, preferably fluorine or chlorine, with an alcohol of theformula VIII ##STR12## wherein n, R⁶, R⁷ and R⁸ are as defined forformula I, in the presence of a base and in a polar aprotic solvent.

The novel compounds of the formula IIa are also obtained by diazotisingamines of the formula IX ##STR13## wherein R¹ and R² are as defined forformula I, and replacing the diazo group with sulfur dioxide in thepresence of a catalyst such as copper chloride, in hydrochloric acid oracetic acid, and reacting the resultant pyridinylsulfonyl chloride ofthe formula X ##STR14## wherein R¹ and R² are as defined for formula I,with ammonium hydroxide solution. The apropriate starting amines areknown or they can be obtained by known procedures.

Likewise, the novel compounds of formula IIa can be obtained byconverting a pyridinylsulfonic acid of the formula XI, ##STR15## whereinR¹ and R² are as defined for formula I, by treatment with a chlorinatingagent such as PCl₅, POCl₃, COCl₂ or SOCl₂, to give the correspondingpyridinylsulfonyl chloride of the formula X, and reacting this chloridewith ammonium hydroxide solution.

The compounds of formula IIa can also be obtained by converting a benzylthioether of the formula XII ##STR16## wherein R¹ and R² are as definedfor formula I, by treatment with chlorine, and reacting the resultantpyridinylsulfonyl chloride of the formula X with ammonium hydroxidesolution.

The pyridinylsulfonyl isocyanates of the formula VI, which are alsonovel, can be obtained by phosgenating the sulfonamides of the formulaIIa, in the presence of butylisocyanate, in a chlorinated hydrocarbon assolvent, at reflux temperature. Similar reactions are described in"Neuere Methoden der praparativen organischen Chemie", Band. VI,211-229, Verlag Chemie, Weinheim, 1970.

The isothiocyanates of the formula VI are obtained by treating thesulfonamides of formula II with carbon disulfide and potassium hydroxideand subsequently phosgenating the dipotassium salt. Such processes aredescribed in Arch. Pharm. 299, 174 (1966).

The N-arylsulfonylcarbamates of the formula IV are obtained by reactingthe sulfonamides of the formula IIa with a carbonate in the presence ofa base. Similar processes are described in Japanese patent specificationNo. 61 169.

The starting aminopyrimidines and aminotriazines of the formula V, aswell as corresponding carbamates of the formula III, have either longbeen known or are described in European patent application No. 70 804,or they can be prepared by known methods from compounds disclosedtherein.

The final products can be isolated by concentrating the reaction mixtureand/or evaporating off the solvent, and purified by recrystallising ortriturating the solid residue in solvents in which they are not readilysoluble, e.g. in an ether, an aromatic hydrocarbon or a chlorinatedhydrocarbon.

The compounds of formula I are stable compounds, and no protectivemeasures are required for handling them.

The compounds of the formulae VII, VIII, IX, X, XI and XII are known orcan be prepared by procedures analogous to known ones.

When used at low rates of application, the compounds of formula I havegood selective growth inhibiting and selective herbicidal propertieswhich make them most suitable for use in crops of useful plants,especially in cereals, cotton, soybeans, maize and rice. In some casesdamage is also caused to weeds which have only been controlled up to nowwith total herbicides.

The mode of action of these compounds is unusual. Many aretranslocatable, i.e. they are absorbed by the plant and transported toother parts of it where they then exert their action. Thus, for example,it is possible to damage perennial weeds to the roots by surfacetreatment. Compared with other herbicides and growth regulators, thenovel compounds of the formula I are effective even when used at verylow rates of application.

The compounds of formula I have in addition pronouncedgrowth-regulating, especially growth-inhibiting, properties. The growthof both monocots and dicots is inhibited. Thus, for example, thecompound of formula I selectively inhibit the growth of leguminosaewhich are frequently planted as cover crops in tropical regions, sothat, while soil erosion between cultivated plants is prevented, thecover crops cannot compete with the cultivated plants.

Inhibition of the vegetative growth of many cultivated plants permitsmore plants to be sown in a crop area, so that a higher yield may beobtained per unit of area. A further mechanism of yield increase usinggrowth regulators resides in the fact that nutrients are ableincreasingly to promote flower formation and fruiting, whereasvegetative growth is inhibited.

At higher rates of application, all tested plants are so severelydamaged in their development that they die.

The invention also relates to herbicidal and growth-regulatingcompositions which contain a novel compound of the formula I, and alsoto methods of controlling weeds pre- and postemergence and of inhibitingthe growth of monocots and dicots, especially grasses, tropical covercrops and tobacco plant suckers.

The compounds of the formula I are used in unmodified form or,preferably, together with the adjuvants conventionally employed in theart of formulation, and are therefore formulated in known manner toemulsifiable concentrates, coatable pastes, directly sprayable ordilutable solutions, dilute emulsions, wettable powders, solublepowders, dusts, granulates, and also encapsulations in e.g. polymersubstances. As with the nature of the compositions, the methods ofapplications, such as spraying, atomising, dusting, scattering orpouring, are chosen in accordance with the intended objectives and theprevailing circumstances.

The formulations, i.e. the compositions containing the compound (activeingredient) of the formula I and, where appropriate, a solid or liquidadjuvant, are prepared in known manner, e.g. by homogeneously mixingand/or grinding the active ingredients with extenders, e.g. solvents,solid carriers and, where appropriate, surface-active compounds(surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractionscontaining 8 to 12 carbon atoms, e.g. xylene mixtures or substitutednaphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate,aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols andglycols and their ethers and esters, such as ethanol, ethylene glycol,ethylene glycol monomethyl or monoethyl ether, ketones such ascyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone,dimethylsulfoxide or dimethylformamide, as well as epoxidised vegetableoils such as epoxidised coconut oil or soybean oil; or water.

The solid carriers used e.g. for dusts and dispersible powders arenormally natural mineral fillers such as calcite, talcum, kaolin,montmorillonite or attapulgite. In order to improve the physicalproperties it is also possible to add highly dispersed silicic acid orhighly dispersed absorbent polymers. Suitable granulated adsorptivecarriers are porous types, for example pumice, broken brick, sepioliteor bentonite; and suitable nonsorbent carriers are materials such ascalcite or sand. In addition, a great number of pregranulated materialsof inorganic or organic nature can be used, e.g. especially dolomite orpulverised plant residues.

Depending on the nature of the compound of the formula I to beformulated, suitable surface-active compounds are nonionic, cationicand/or anionic surfactants having good emulsifying, dispersing andwetting properties. The term "surfactants" will also be understood ascomprising mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps andwater-soluble synthetic surface-active compounds.

Suitable soaps are the alkali metal salts, alkaline earth metal salts orunsubstituted or substituted ammonium salts or higher fatty acids (C₁₀-C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid, orof natural fatty acid mixtures which can be obtained e.g. from coconutoil or tallow oil. Mention may also be made of fatty acid methyltaurinsalts.

More frequently, however, so-called synthetic surfactants are used,especially fatty sulfonates, fatty sulfates, sulfonated benzimidazolederivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are usually in the form of alkali metalsalts, alkaline earth metal salts or unsubstituted or substitutedammonium salts and contain a C₈ -C₂₂ alkyl radical which also includesthe alkyl moiety of acyl radicals, e.g. the sodium or calcium salt oflignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcoholsulfates obtained from natural fatty acids. These compounds alsocomprise the salts of sulfuric acid esters and sulfonic acids of fattyalcohol/ethylene oxides adducts. The sulfonated benzimidazolederivatives preferably contain 2 sulfonic acid groups and one fatty acidradical containing 8 to 22 carbon atoms. Examples of alkylarylsulfonatesare the sodium, calcium or triethylanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of anaphthalenesulfonic acid/formaldehyde condensation product. Alsosuitable are corresponding phosphates, e.g. salts of the phosphoric acidester of an adduct of p-nonylphenol with 4 to 14 moles of ethyleneoxide, or phospholipids.

Non-ionic surfactants are preferably polyglycol ether derivatives ofaliphatic or cycloaliphatic alcohols, or saturated or unsaturated fattyacids and alkylphenols, said derivatives containing 3 to 30 glycol ethergroups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moietyand 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts ofpolyethylene oxide with polypropylene glycol, ethylenediamine propyleneglycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms inthe alkyl chain, which adducts contain 20 to 250 ethylene glycol ethergroups and 10 to 100 propylene glycol ether groups. These compoundsusually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Representative examples of non-ionic surfactants arenonylphenolpolyethoxyethanols, castor oil polyglycol ethers,polypropylene/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol andoctylphenoxyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitanand polyoxyethylene sorbitan trioleate are also suitable non-ionicsurfactants.

Cationic surfactants are preferably quaternary ammonium salts whichcontain, as N-substituent, at least one C₈ -C₂₂ alkyl radical and, asfurther substituents, lower unsubstituted or halogenated alkyl, benzylor lower hydroxyalkyl radicals. The salts are preferably in the form ofhalides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammoniumchloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in the art of formulation aredescribed e.g. in the following publications:

"McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp.,Ridgewood, N.J., 1981; H. Stache, "Tensid-Taschenbuch", 2nd Edition, C.Hanser Verlag, Munich & Vienna, 1981; M. and J. Ash, "Encyclopedia ofSurfactants", Vol. I-III, Chemical Publishing Co., New York, 1980-81.

The pesticidal compositions usually contain 0.1 to 95%, preferably 0.1to 80%, of a compound of the formula I, 1 to 99.9%, of a solid or liquidadjuvant, and 0 to 25%, preferably 0.1 to 25%, of a surfactant.

Preferred formulations are composed in particular of the followingconstituents (%=percentage by weight):

    ______________________________________                                        Emulsifiable concentrates                                                     active ingredient:                                                                           1 to 20%,  preferably 5 to 10%                                 surfactant:    5 to 30%,  preferably 10 to 20%                                liquid carrier:                                                                              50 to 94%, preferably 70 to 85%                                Dusts                                                                         active ingredient:                                                                           0.1 to 10%,                                                                              preferably 0.1 to 1%                                solid carrier: 99.9 to 90%,                                                                             preferably 99.9 to 99%                              Suspension concentrates                                                       active ingredient:                                                                           5 to 75%,  preferably 10 to 50%                                water:         94 to 25%, preferably 90 to 30%                                surfactant:    1 to 40%,  preferably 2 to 30%                                 Wettable powders                                                              active ingredient:                                                                           0.5 to 90%,                                                                              preferably 1 to 80%                                 surfactant:    0.5 to 20%,                                                                              preferably 1 to 15%                                 solid carrier: 5 to 95%,  preferably 15 to 90%                                Granulates                                                                    active ingredient:                                                                           0.5 to 30%,                                                                              preferably 3 to 15%                                 solid carrier: 99.5 to 70%,                                                                             preferably 97 to 85%.                               ______________________________________                                    

Whereas commercial products will be preferably formulated asconcentrates, the end user will normally employ dilute formulations. Theformulations can be diluted to a concentration as low as 0.001% Therates of application are normally from 0.01 to 10 kg a.i./ha, preferablyfrom 0.025 to 5 kg a.i./ha.

The compositions may also contain further ingredients such asstabilisers, antifoams, viscosity regulators, binders, tackifiers, aswell as fertilisers and other compounds for obtaining special effects.

The invention is illustrated by the following Examples.

EXAMPLE P1N-(2-Cyclopentyloxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea(compound 5.1)

(a) 2-Cyclopentyloxypyridin-3-ylsulfonamide

10.9 g of a 55% dispersion of sodium hydride are suspended in 40 ml ofdimethylformamide and then 13.6 ml of cyclopentanol are added dropwise.Then a solution of 19.24 g of 2-chloropyridin-3-ylsulfonamide in 40 mlof dimethylformamide is added dropwise and the reaction mixture isstirred for 2 hours at 35°-40° C. and then taken up in a mixture of 250ml of ethyl acetate, 250 ml of ice-water and 125 ml of 1N hydrochloricacid. After extraction with 3×100 ml of ethyl acetate the combinedorganic phases are washed with 4×100 ml of water. The organic solutionis washed and dried, affording an oily residue which crystallises aftertrituration with 50 ml of ether to give 19.64 g of2-cyclopentyloxypyridin-3-ylsulfonamide with a melting point of134°-135° C.

(b) To a mixture of 4.84 g of 2-cyclopentyloxypyridin-3-ylsulfonamideand 3.13 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene in 50 ml of absolutedioxan are added 5.46 g ofN-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)phenylcarbamate at 20° to 25°C. The mixture is stirred for 1/2 hour, the precipitate is isolated andthe filtrate is concentrated by evaporation. The residue is trituratedwith 10 ml of 2N hydrochloric acid and the crystals so obtained areisolated, washed with ether and water and dried, affording 7.79 g ofN-(2-cyclopentyloxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureawith a melting point of 170°-172° C.

EXAMPLE P2N-(2-Cyclopropylmethoxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea(compound 5.60)

(a) 2-Cyclopropylmethoxypyridin-3-ylsulfonamide

11.99 g of a 55% dispersion of sodium hydride are suspended in 40 ml ofdimethylformamide and 13.04 ml of cyclopropylmethanol are added dropwiseat 10° C. under a nitrogen atmosphere. The mixture is stirred for 15minutes and then a solution of 21.16 g of2-chloropyridin-3-ylsulfonamide in 40 ml of dimethylformamide is addeddropwise. The reaction mixture is stirred for 30 minutes at 35°-40° C.and then taken up in a mixture of 275 ml of ethyl acetate, 275 ml oficewater and 137.5 ml of 2N hydrochloric acid. The organic phase isseparated and the aqueous phase is extracted with 3×100 ml of ethylacetate. The combined organic phases are washed with 4×100 ml of water,dried, concentrated by evaporation and the residue is triturated withether/hexane (2:1). The crystals so obtained are isolated and dried,affording 22.25 g of 2-cyclopropylmethoxypyridin-3-ylsulfonamide with amelting point of 121°-122° C.

(b) 4.56 g of 2-cyclopropylmethoxypyridin-3-ylsulfonamide and 3.13 ml of1,8-diazabicyclo[5.4.0]undec-7-ene are suspended in 50 ml of dioxan andto this suspension are added 5.46 g ofN-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)phenylcarbamate. The mixture isstirred for 20 minutes and concentrated by evaporation. The residue istriturated with 10 ml of 2N hydrochloric acid and the precipitated solidis isolated and washed with water and ether, affording 6.90 g ofN-(2-cyclopropylmethoxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureawith a melting point of 165°-167° C.

The compounds of intermediates listed in the following tables areobtained in an analogous manner.

                  TABLE 1                                                         ______________________________________                                         ##STR17##                                                                    Compound                                                                              R.sup. 2                                                                             T             Y                                                ______________________________________                                        1.1     H      2-oxocyclopentyl                                                                            NH.sub.2                                         1.2     H      2-oxocyclopentyl                                                                            NHCONHCH.sub.3                                   1.3     H      2-oxocyclopentyl                                                                            NCO                                              1.4     H      2-cyclopentenyl                                                                             NH.sub.2                                         1.5     H      2-cyclopentenyl                                                                             NHCONHCH.sub.3                                   1.6     H      2-cyclopentenyl                                                                             NCO                                              1.7     H      2-cyclohexenyl                                                                              NH.sub.2                                         1.8     H      2-cyclohexenyl                                                                              NHCONHCH.sub.3                                   1.9     H      2-cyclohexenyl                                                                              NCO                                               1.10   H      2-cyclohexenyl                                                                              NHCOOC.sub.6 H.sub.5                             ______________________________________                                    

                                      TABLE 2                                     __________________________________________________________________________     ##STR18##                                                                                 Position Position                                                Com-         of OT    of SO.sub.2Y                                                                         Physical                                         pound                                                                             R.sup.2                                                                         T      radical                                                                             Y  radical                                                                              data                                             __________________________________________________________________________    2.1 H cyclopentyl                                                                          2     NH.sub.2                                                                         3      m.p. 134-135° C.                          2.2 H cyclohexyl                                                                           2     NH.sub.2                                                                         3      m.p. 146-147° C.                          2.3 H cyclopropyl-                                                                         2     NH.sub.2                                                                         3      m.p. 121-122° C.                                methyl                                                                  2.4 H 1-methyl-                                                                            2     NH.sub.2                                                                         3                                                             cyclopropyl                                                             2.5 H cyclopentyl-                                                                         2     NH.sub.2                                                                         3                                                             methyl                                                                  2.6 H 2-chloro-                                                                            2     NH.sub.2                                                                         3                                                             cyclopentyl                                                             2.7 H cyclopentyl                                                                          3     NH.sub.2                                                                         2                                                       __________________________________________________________________________

                  TABLE 3                                                         ______________________________________                                         ##STR19##                                                                    Compound                                                                              T            R.sup.2                                                                             R.sup.3                                                                           R.sup.4                                                                             R.sup.5 X                                ______________________________________                                        3.1     2-cyclopentenyl                                                                            H     H   CH.sub.3                                                                            OCH.sub.3                                                                             O                                3.2     2-cyclopentenyl                                                                            H     H   OCH.sub.3                                                                           OCH.sub.3                                                                             O                                3.3     2-cyclopentenyl                                                                            H     H   C.sub.2 H.sub.5                                                                     OCH.sub.3                                                                             O                                3.4     2-cyclopentenyl                                                                            H     H   CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                      O                                3.5     2-cyclopentenyl                                                                            H     H   OCH.sub.3                                                                           OCH.sub.2 CF.sub.3                                                                    O                                3.6     2-cyclopentyl-                                                                             H     H   OCH.sub.3                                                                           OCH.sub.3                                                                             O                                        methyl                                                                3.7     2-oxocyclopentyl                                                                           H     H   CH.sub.3                                                                            OCH.sub.3                                                                             O                                ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                         ##STR20##                                                                    Compound                                                                              T            R.sup.2                                                                             R.sup.3                                                                           R.sup.4                                                                             R.sup.5 X                                ______________________________________                                        4.1     2-cyclopentenyl                                                                            H     H   CH.sub.2                                                                            OCH.sub.3                                                                             O                                4.2     2-cyclopentenyl                                                                            H     H   OCH.sub.3                                                                           OCH.sub.3                                                                             O                                4.3     2-cyclopentenyl                                                                            H     H   Cl    OCH.sub.3                                                                             O                                4.4     2-cyclopentenyl                                                                            H     H   CH.sub.3                                                                            OCHF.sub.2                                                                            O                                4.5     2-cyclopentenyl                                                                            H     H   OCH.sub.3                                                                           OCHF.sub.2                                                                            O                                4.6     2-oxocyclopentyl                                                                           H     H   CH.sub.3                                                                            OCH.sub.3                                                                             O                                4.7     2-oxocyclopentyl                                                                           H     H   OCH.sub.3                                                                           OCH.sub.3                                                                             O                                ______________________________________                                    

                                      TABLE 5                                     __________________________________________________________________________     ##STR21##                                                                                     Position                     Position                                         of OT                        of SO.sub.2                                                                         m.p.                      Compound                                                                            T          radical                                                                             R.sup.2                                                                             R.sup.3                                                                          R.sup.4                                                                            R.sup.5                                                                              X radical                                                                             [°C.]              __________________________________________________________________________    5.1   cyclopentyl                                                                              2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3     170-172                   5.2   cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3     192-194                   5.3   cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.4   cyclopentyl                                                                              2     H     H  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     O 3                               5.5   cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                     O 3                               5.6   cyclopentyl                                                                              2     H     H  CH.sub.3                                                                           OCH(CH.sub.3).sub.2                                                                  O 3                               5.7   cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          C.sub.2 H.sub.5                                                                      O 3                               5.8   cyclopentyl                                                                              2     H     H  CH.sub.3                                                                           C.sub.2 H.sub.5                                                                      O 3                               5.9   cyclopentyl                                                                              2     H     H  N(CH.sub.3).sub.2                                                                  OCH.sub.2 CF.sub.3                                                                   O 3                               5.10  cyclopentyl                                                                              2     H     H  CH.sub.3                                                                           SCHF.sub.2                                                                           O 3                               5.11  cyclohexyl 2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3     154-155                   5.12  cyclohexyl 2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3     170-172                   5.13  cyclohexyl 2     H     H  C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                            O 3                               5.14  cyclohexyl 2     H     H  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     O 3                               5.15  cyclohexyl 2     H     H  OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                   O 3                               5.16  cyclobutyl 2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.17  cyclobutyl 2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.18  cyclobutyl 2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.19  cyclobutyl 2     H     H  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     O 3                               5.20  cyclobutyl 2     H     H  OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                   O 3                               5.21  cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                    O 3                               5.22  cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          NHCH.sub.3                                                                           O 3                               5.23  cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          cyclopropyl                                                                          O 3                               5.24  cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          SCH.sub.3                                                                            O 3                               5.25  cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                   O 3                               5.26  cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          CH.sub.2 F                                                                           O 3                               5.27  cyclopentyl                                                                              2     H     H  CH.sub.3                                                                           CH.sub.2 Cl                                                                          O 3                               5.28  cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          CH.sub.2 Cl                                                                          O 3                               5.29  cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                   O 3                               5.30  cyclopentyl                                                                              2     H     H  CH.sub.3                                                                           OCH.sub.2 CF.sub.3                                                                   O 3                               5.31  cyclopentyl                                                                              2     H     H  CH.sub.3                                                                           CH.sub.3                                                                             O 3                               5.32  cyclopentyl                                                                              2     H     H  Cl   CH.sub.3                                                                             O 3                               5.33  2-cyclopentenyl                                                                          2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.34  2-cyclopentenyl                                                                          2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.35  2-cyclopentenyl                                                                          2     H     H  C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                            O 3                               5.36  2-cyclopentenyl                                                                          2     H     H  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     O 3                               5.37  cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                   O 3                               5.38  2-cholrocyclopentyl                                                                      2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.39  2-chlorocyclopentyl                                                                      2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.40  2-chlorocyclopentyl                                                                      2     H     H  C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                            O 3                               5.41  2-chlorocyclopentyl                                                                      2     H     H  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     O 3                               5.42  2-chlorocyclopentyl                                                                      2     H     H  OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                   O 3                               5.43  2-fluorocyclopentyl                                                                      2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.44  2-fluorocyclopentyl                                                                      2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.45  cyclopentyl                                                                              2     5-F   H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.46  cyclopentyl                                                                              2     5-H   H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.47  cyclopentyl                                                                              2     5-Cl  H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.48  cyclopentyl                                                                              2     5-Cl  H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.49  cyclopentyl                                                                              2     5-OCH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.50  cyclopentyl                                                                              2     5-OCH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.51  cyclopentyl                                                                              2     5-NO.sub.2                                                                          H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.52  cyclopentyl                                                                              2     5-NO.sub.2                                                                          H  OCH.sub.3                                                                          OCH.sub. 3                                                                           O 3                               5.53  cyclopentyl                                                                              2     6-Cl  H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.54  cyclopentyl                                                                              2     6-Cl  H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.55  cyclopentyl                                                                              2     6-COOCH.sub.3                                                                       H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.56  cyclopentyl                                                                              2     6-COOCH.sub.3                                                                       H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.57  cyclopentyl                                                                              2     H     CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.58  cyclopentyl                                                                              2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            S 3                               5.59  cyclopentyl                                                                              2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            S 3                               5.60  cyclopropylmethyl                                                                        2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3     165-167                   5.61  cyclopropylmethyl                                                                        2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3     164-165                   5.62  cyclopropylmethyl                                                                        2     H     H  C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                            O 3                               5.63  cyclopropylmethyl                                                                        2     H     H  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     O 3                               5.64  cyclopropylmethyl                                                                        2     H     H  OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                   O 3                               5.65  1-methylcyclopropyl                                                                      2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.66  1-methylcyclopropyl                                                                      2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.67  cyclohexylmethyl                                                                         2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.68  cyclohexylmethyl                                                                         2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.69  cyclopentylmethyl                                                                        2     H     H  CH.sub.3                                                                           OCH.sub. 3                                                                           O 3                               5.70  cyclopentylmethyl                                                                        2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.71  2-oxocyclopentyl                                                                         2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.72  2-oxocyclopentyl                                                                         2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.73  2-methoxycyclopentyl                                                                     2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.74  2-methoxycyclopentyl                                                                     2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.75  1-methylcyclopentyl                                                                      2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                               5.76  2-cyanocyclopentyl                                                                       2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.77  cyclopentyl                                                                              3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                               5.78  cyclopentyl                                                                              3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                               5.79  cyclohexyl 3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                               5.80  cyclohexyl 3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                               5.81  2-cyclopentenyl                                                                          3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                               5.82  2-cyclopentenyl                                                                          3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                               5.83  2-chlorocyclopentyl                                                                      3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                               5.84  2-chlorocyclopentyl                                                                      3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                               5.85  cyclopropylmethyl                                                                        3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                               5.86  cyclohexylmethyl                                                                         2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                               5.87  cyclohexylmethyl                                                                         3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                               5.88  cyclohexylmethyl                                                                         3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                               __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________     ##STR22##                                                                                   Position                     Position                                         of OT                        of SO.sub.2                                                                         m.p.                        Compound                                                                            T        radical                                                                             R.sup.2                                                                             R.sup.3                                                                          R.sup.4                                                                            R.sup.5                                                                              X radical                                                                             [°C.]                __________________________________________________________________________    6.1   cyclopentyl                                                                            2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.2   cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3     180-182                     6.3   cyclopentyl                                                                            2     H     H  Cl   OCH.sub.3                                                                            O 3                                 6.4   cyclopentyl                                                                            2     H     H  CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     O 3                                 6.5   cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                     O 3                                 6.6   cyclopentyl                                                                            2     H     H  CH.sub.3                                                                           OCHF.sub.2                                                                           O 3     161-163                     6.7   cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          OCHF.sub.2                                                                           O 3                                 6.8   cyclopentyl                                                                            2     H     H  OCHF.sub.2                                                                         OCHF.sub.2                                                                           O 3                                 6.9   cyclopentyl                                                                            2     H     H  N(CH.sub.3).sub.2                                                                  OCHF.sub.2                                                                           O 3                                 6.10  cyclopentyl                                                                            2     H     H  Cl   OCHF.sub.2                                                                           O 3                                 6.11  cyclohexyl                                                                             2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.12  cyclohexyl                                                                             2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3     196-199                     6.13  cyclohexyl                                                                             2     H     H  Cl   OCH.sub.3                                                                            O 3                                 6.14  cyclohexyl                                                                             2     H     H  CH.sub.3                                                                           OCHF.sub.2                                                                           O 3     169-171                     6.15  cyclohexyl                                                                             2     H     H  OCH.sub.3                                                                          OCHF.sub.2                                                                           O 3                                 6.16  cyclobutyl                                                                             2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.17  cyclobutyl                                                                             2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                 6.18  cyclobutyl                                                                             2     H     H  Cl   OCH.sub.3                                                                            O 3                                 6.19  cyclobutyl                                                                             2     H     H  CH.sub.3                                                                           OCHF.sub.2                                                                           O 3                                 6.20  cyclobutyl                                                                             2     H     H  OCH.sub.3                                                                          OCHF.sub.2                                                                           O 3                                 6.21  cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                    O 3                                 6.22  cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          NHCH.sub. 3                                                                          O 3                                 6.23  cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          cyclopropyl                                                                          O 3                                 6.24  cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          SCH.sub.3                                                                            O 3                                 6.25  cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                   O 3                                 6.26  cyclopentyl                                                                            2     H     H  OCHF.sub.2                                                                         CH.sub.2 F                                                                           O 3                                 6.27  cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          CH.sub.2 F                                                                           O 3                                 6.28  cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          CH.sub.2 Cl                                                                          O 3                                 6.29  cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                   O 3                                 6.30  cyclopentyl                                                                            2     H     H  CH.sub.3                                                                           OCH.sub.2 CF.sub.3                                                                   O 3                                 6.31  cyclopentyl                                                                            2     H     H  CH.sub.3                                                                           CH.sub.3                                                                             O 3                                 6.32  cyclopentyl                                                                            2     H     H  Cl   CH.sub.3                                                                             O 3                                 6.33  2-cyclopentenyl                                                                        2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.34  2-cyclopentenyl                                                                        2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                 6.35  2-cyclopentenyl                                                                        2     H     H  Cl   OCH.sub.3                                                                            O 3                                 6.36  2-cyclopentenyl                                                                        2     H     H  CH.sub.3                                                                           OCHF.sub.2                                                                           O 3                                 6.37  2-cyclopentenyl                                                                        2     H     H  OCH.sub.3                                                                          OCHF.sub.2                                                                           O 3                                 6.38  2-chlorocyclo-                                                                         2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                       pentyl                                                                  6.39  2-chlorocyclo-                                                                         2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                       pentyl                                                                  6.40  2-chlorocyclo-                                                                         2     H     H  Cl   OCH.sub.3                                                                            O 3                                       pentyl                                                                  6.41  2-chlorocyclo-                                                                         2     H     H  CH.sub.3                                                                           OCHF.sub.2                                                                           O 3                                       pentyl                                                                  6.42  2-chlorocyclo-                                                                         2     H     H  OCH.sub.3                                                                          OCHF.sub.2                                                                           O 3                                       pentyl                                                                  6.43  2-fluorocyclo-                                                                         2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                       pentyl                                                                  6.44  2-fluorocyclo-                                                                         2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                       pentyl                                                                  6.45  cyclopentyl                                                                            2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.46  cyclopentyl                                                                            2     5-F   H  OCH.sub.3                                                                          OCH.sub.3                                  6.47  cyclopentyl                                                                            2     5-Cl  H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.48  cyclopentyl                                                                            2     5-Cl  H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                 6.49  cyclopentyl                                                                            2     5-OCH.sub.3                                                                         H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.50  cyclopentyl                                                                            2     5-OCH.sub.3                                                                         H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                 6.51  cyclopentyl                                                                            2     5-NO.sub.2                                                                          H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.52  cyclopentyl                                                                            2     5-NO.sub.2                                                                          H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                 6.53  cyclopentyl                                                                            2     6-Cl  H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.54  cyclopentyl                                                                            2     6-Cl  H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                 6.55  cyclopentyl                                                                            2     6-COOCH.sub.3                                                                       H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.56  cyclopentyl                                                                            2     6-COOCH.sub.3                                                                       H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                 6.57  cyclopentyl                                                                            2     H     CH.sub.3                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                 6.58  cyclopentyl                                                                            2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            S 3                                 6.59  cyclopentyl                                                                            2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            S 3                                 6.60  cyclopropyl-                                                                           2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                       methyl                                                                  6.61  cyclopropyl-                                                                           2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3     167-168                           methyl                                                                  6.62  cyclopropyl-                                                                           2     H     H  Cl   OCH.sub.3                                                                            O 3                                       methyl                                                                  6.63  cyclopropyl-                                                                           2     H     H  CH.sub.3                                                                           OCHF.sub.2                                                                           O 3     156-158                           methyl                                                                  6.64  cyclopropyl-                                                                           2     H     H  OCH.sub.3                                                                          OCHF.sub.2                                                                           O 3                                       methyl                                                                  6.65  1-methylcyclo-                                                                         2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                       propyl                                                                  6.66  1-methylcyclo-                                                                         2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                       propyl                                                                  6.67  cyclohexyl-                                                                            2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                       methyl                                                                  6.68  cyclohexyl-                                                                            2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                       methyl                                                                  6.69  cyclopentyl-                                                                           2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                       methyl                                                                  6.70  cyclopentyl-                                                                           2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                       methyl                                                                  6.71  2-oxocyclopentyl                                                                       2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                 6.72  2-oxocyclopentyl                                                                       2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                 6.73  2-methoxycyclo-                                                                        2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                       pentyl                                                                  6.74  1-methoxycyclo-                                                                        2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                       pentyl                                                                  6.75  2-cyanocyclo-                                                                          2     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 3                                       pentyl                                                                  6.76  2-cyanocyclo-                                                                          2     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 3                                       pentyl                                                                  6.77  cyclopentyl                                                                            3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                                 6.78  cyclopentyl                                                                            3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                                 6.79  cyclohexyl                                                                             3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                                 6.80  cyclohexyl                                                                             3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                                 6.81  2-cyclopentenyl                                                                        3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                                 6.82  2-cyclopentyl                                                                          3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                                 6.83  2-chlorocyclo-                                                                         3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                                       pentyl                                                                  6.84  2-chlorocyclo-                                                                         3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                                       pentyl                                                                  6.85  cyclopropyl-                                                                           3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                                       methyl                                                                  6.86  cyclopropyl-                                                                           3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                                       methyl                                                                  6.87  cyclopropyl-                                                                           3     H     H  CH.sub.3                                                                           OCH.sub.3                                                                            O 2                                       methyl                                                                  6.88  cyclopropyl-                                                                           3     H     H  OCH.sub.3                                                                          OCH.sub.3                                                                            O 2                                       methyl                                                                  6.89  cyclohexyl                                                                             2     H     H  OCHF.sub.2                                                                         OCHF.sub.2                                                                           O 3                                 6.90  cyclopentyl                                                                            2     H     H  OCHF.sub.2                                                                         OCHF.sub.2                                                                           O 3                                 6.91  2-cyclopentenyl                                                                        2     H     H  OCHF.sub.2                                                                         OCHF.sub.2                                                                           O 3                                 6.92  2-chlorocyclo-                                                                         2     H     H  OCHF.sub.2                                                                         OCHF.sub.2                                                                           O 3                                       pentyl                                                                  6.93  cyclopropyl-                                                                           2     H     H  OCHF.sub.2                                                                         OCHF.sub.2                                                                           O 3                                       methyl                                                                  __________________________________________________________________________

FORMULATION EXAMPLES Example F1 Formulation Examples for compounds offormula I (percentages are by weight)

    ______________________________________                                        (a) Wettable powders                                                                              (a)     (b)     (c)                                       ______________________________________                                        Compound of formula I                                                                             20%     60%     0.5%                                      sodium lignosulfonate                                                                              5%      5%      5%                                       sodium laurylsulfate                                                                               3%     --      --                                        sodium diisobutylnaphthalenesulfonate                                                             --       6%      6%                                       octylphenol polyethylene glycol ether                                                             --       2%      2%                                       (7-8 moles of ethylene oxide)                                                 highly dispersed silicid acid                                                                      5%     27%     27%                                       kaolin              67%     --      --                                        sodium chloride     --      --      59.5%                                     ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders which can be diluted with water to give suspensions of thedesired concentration.

    ______________________________________                                        (b) Emulsifiable concentrates                                                                        (a)    (b)                                             ______________________________________                                        Compound of formula I  10%     1%                                             octylphenol polyethylene glycol ether                                                                 3%     3%                                             (4-5 moles of ethylene oxide)                                                 calcium dodecylbenzenesulfonate                                                                       3%     3%                                             castor oil polyglycol ether                                                                           4%     4%                                             (36 moles of ethylene oxide)                                                  cyclohexanone          30%    10%                                             xylene mixture         50%    79%                                             ______________________________________                                    

Emulsions of any required concentration can be obtained from thisconcentrate by dilution with water.

    ______________________________________                                        (c) Dusts           (a)     (b)                                               ______________________________________                                        Compound of formula I                                                                              0.1%    1%                                               talcum              99.9%   --                                                kaolin              --      99%                                               ______________________________________                                    

Dusts which are ready for use are obtained by mixing the activeingredient with the carriers, and grinding the mixture in a suitablemill.

    ______________________________________                                        (d) Extruder granulate                                                                            (a)    (b)                                                ______________________________________                                        Compound of formula I                                                                             10%     1%                                                sodium lignosulfonate                                                                              2%    2%                                                 carboxymethylcellulose                                                                             1%    1%                                                 kaolin              87%    96%                                                ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants, and themixture is subsequently moistened with water. The mixture is extrudedand then dried in a stream of air.

    ______________________________________                                        (e) Coated granulate                                                          ______________________________________                                        Compound of formula                                                                              3%                                                         polyethylene glycol 200                                                                          2%                                                         kaolin             94%                                                        ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coatedgranulates are obtained in this manner.

    ______________________________________                                        (f) Suspension concentrate                                                                           (a)     (b)                                            ______________________________________                                        Compound of formula I  40%      5%                                            ethylene glycol        10%     10%                                            nonylphenol polyethylene glycol ether                                                                 6%      1%                                            (15 moles of ethylene oxide)                                                  sodium lignosulfonate  10%      5%                                            carboxymethylcellulose  1%      1%                                            37% aqueous formaldehyde solution                                                                    0.2%    0.2%                                           silicone oil in the form of a 75%                                                                    0.8%    0.8%                                           aqueous emulsion                                                              water                  32%     77%                                            ______________________________________                                    

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired concentration can be obtained by dilution with water.

    ______________________________________                                        (g) Salt solution                                                             ______________________________________                                        Compound of formula I  5%                                                     isopropylamine         1%                                                     octylphenol polyethylene glycol ether                                                                3%                                                     (78 moles of ethylene oxide)                                                  water                  91%                                                    ______________________________________                                    

BIOLOGICAL EXAMPLES Example B1 Preemergence herbicidal action

Plastic pots are filled with expanded vermiculite (density: 0.135 g/cm³,water-absorbing capacity: 0.565 l/l). After the non-adsorptivevermiculite has been saturated with an aqueous emulsion in deionisedwater which contains the test compound in a concentration of 70.8 ppm,seeds of the following plants are sown on the surface: Nasturtiumofficinalis, Agrostis tenuis, Stellaria media and Digitaria sanguinalis.The pots are then kept in a climatic chamber at 20° C., an illuminationof about 20 klux and a relative humidity of 70%. During the germinatingphase of 4 to 6 days, the pots are covered with lightpermeable materialand watered with deionised water to increase the local humidity. Afterthe 5th day, 0.5% of a commercial liquid fertiliser (Greenzit®, exCiba-Geigy) is added to the water. The test is evaluated 12 days aftersowing and the action on the plants is assessed according to thefollowing rating:

1: plants have not emerged or are totally withered

2-3: very pronounced action

4-6: medium action

7-8: weak action

9: no action (as untreated controls).

Preemergence action

Concentration of the test compound emulsion: 70.8 ppm

    ______________________________________                                        Test plant                                                                    Compound                                                                              Nasturtium Stellaria Agrostis                                                                              Digitaria                                ______________________________________                                        5.1     2          2         2       2                                        5.2     2          2         2       2                                        5.11    2          2         3       2                                        5.12    2          2         2       3                                        5.60    2          2         2       2                                        5.61    2          2         2       2                                        6.2     1          1         1       1                                        6.6     2          2         2       2                                        6.12    2          2         2       2                                        6.14    2          2         2       2                                        6.61    2          2         2       2                                        6.63    2          2         2       2                                        ______________________________________                                    

EXAMPLE B2 Growth inhibition of tropical cover crops

The test plants (centrosema plumieri and centrosema pubescens) arereared until fully grown and then cut back to a height of 60 cm. Theplants are sprayed 7 days later with an aqueous emulsion of the testcompound. The test plants are kept at 70% relative humidity and 6000 luxartificial light for 14 hours per day, at day temperatures of 27° C. andnight temperatures of 21° C. The test is evaluated 4 weeks afterapplication by assessing and weighing the new growth compared withcontrols and by determining the phytotoxicity.

In this test a marked reduction in new growth of the plants treated withcompounds of the formula I is observed (less than 20% of the new growthof untreated control plants), without damage being caused to the testplants.

EXAMPLE B3 Growth regulation of soybeans

Soybeans of the "Hark" variety are sown in plastic containers in anearth/peat/sand mixture (6:3:1). The containers are put into a climaticchamber and the plants develop to the 5-6 trefoil leaf stage after about5 weeks by optimum control of temperature, light, fertiliser addition,and watering. The plants are then sprayed with an aqueous mixture of acompound of the formula I until thoroughly wetted. The rate ofapplication corresponds to 100 g a.i. per hectare. Evaluation is madeabout 5 weeks after application. Compared with untreated controls, thecompounds of the formula I markedly increase the number and weight ofthe harvested siliques on the leading shoot.

EXAMPLE B4 Growth inhibition of cereals

Summar barley (Hordeum vulgare) and summer rye (Secale) are sown insterilised soil in plastic beakers in a greenhouse and watered asrequired. The cereal shoots are treated about 21 days after sowing withan aqueous spray mixture of a compound of the formula I. Theconcetration corresponds to 100 g of active ingredient per hectare.Evaluation of the growth of the cereals is made 21 days afterapplication. A comparison with untreated controls shows that the growthof cereal plants treated with compounds of the formula I issignificantly reduced (60-90% of the controls) and that the diameter ofthe stalks has in some cases increased.

EXAMPLE B5 Growth inhibition of grasses

Seeds of the grasses Lolium perenne, Poa pratensis, Festuca ovina,Dactylis glomerate and Cynodon dactylon are sown in plastic dishesfilled with an earth/peat/sand mixture (6:3:1), in a greenhouse, andwatered as required. The emergent grasses are cut back weekly to aheight of 4 cm, and about 50 days after sowing and 1 day after the lastcut are sprayed with an aqueous spray mixture of a compound of theformula I. The concentration of test compound corresponds to a rate ofapplication of up to 100 g a.i. per hectare. The growth of the grassesis evaluated 21 days after application. The compounds of formula Ieffect a reduction in new growth in the range of 10-30% in comparisonwith untreated controls.

What is claimed is:
 1. An N-arylsulfonyl-N'-triazinylurea of the formulaI ##STR23## wherein R¹ is a ##STR24## R² is hydrogen, halogen, nitro, C₁-C₃ alkyl, C₁ -C₃ alkoxy or --COOR⁹,R³ is hydrogen, C₁ -C₃ alkyl or C₁-C₃ alkoxy, R⁴ and R⁵ are each independently of the other hydrogen,halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ haloalkylthio, C₂ -C₄ alkoxyalkyl,C₃ -C₆ -cycloalkyl or --NR¹⁰ R¹¹, R⁶ is hydrogen or C₁ -C₃ alkyl, R⁷ ishydrogen or methyl, R⁸ is C₄ -C₆ cycloalkanonyl which is unsubstitutedor substituted by C₁ -C₃ alkyl or halogen; C₃ -C₆ cycloalkyl which isunsubstituted or substituted by one or more identical or differentmembers selected from the group consisting of C₁ -C₃ alkyl, C₁ -C₃alkoxy, halogen or cyano; or is C₅ -C₆ cycloalkenyl which isunsubstituted or substituted by C₁ -C₃ alkyl, halogen or cyano, R⁹ is C₁-C₃ alkyl or allyl, R¹⁰ and R¹¹ are each independently of the otherhydrogen or C₁ -C₄ -alkyl, n is 0 or 1, X is sulfur or oxygen, and E isnitrogen and Z is nitrogen or the methine bridge, with the proviso thatR⁸ is only unsubstituted or substituted C₃ -C₆ cycloalkyl if at the sametime Z is nitrogen,or a salt thereof.
 2. A compound according to claim1, wherein Z is nitrogen.
 3. A compound according to claim 2, wherein Xis oxygen and Z is nitrogen, R² and R³ are hydrogen, R⁴ and R⁵ are eachindependently of the other C₁ -C₃ alkyl, halogen, C₁ -C₃ alkoxy, di(C₁-C₃)alkylamino or C₁ -C₃ haloalkoxy, and together contain not more than4 carbon atoms, and R¹ is cyclopentyloxy or cyclohexyloxy.
 4. A compoundaccording to claim 2, wherein X is oxygen.
 5. A compound according toclaim 2, wherein R² is hydrogen.
 6. A compound according to claim 2,wherein R³ is hydrogen.
 7. A compound according to claim 2, wherein R¹is --O--CHR⁷ -cyclopropyl.
 8. A compound according to claim 2, whereinR⁴ and R⁵ are each independently halogen, C₁ -C₃ alkyl, C₁ -C₃ alkoxy,di(C₁ -C₃)alkylamino or C₁ -C₃ haloalkoxy, and together contain not morethan 4 carbon atoms.
 9. A compound according to claim 2, wherein X isoxygen, R² and R³ is hydrogen, R⁴ and R⁵ are each independently of theother halogen, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, di(C₁ -C₃)alkylamino or C₁-C₃ haloalkoxy, and together contain not more than 4 carbon atoms, Z isnitrogen and R¹ is an --O--R⁸ radical.
 10. A compound according to claim2, wherein X is oxygen and Z is nitrogen, R² and R³ are hydrogen, R⁴ andR⁵ are each independently of the other C₁ -C₃ alkyl, halogen, C₁ -C₃alkoxy, di(C₁ -C₃)alkylamino or C₁ -C₃ haloalkoxy, and together containnot more than 4 carbon atoms, and R¹ is C₃ -C₆ cycloalkoxy.
 11. Acompound according to claim 2, wherein R¹ is --O--R⁸.
 12. A compoundaccording to claim 6, wherein R⁸ is C₃ -C₆ cycloalkyl.
 13. A compoundaccording to claim 11, wherein R⁸ is cyclopentyl or cyclohexyl. 14.N-(2-cyclopentyloxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaaccording to claim
 2. 15.N-(2-cyclopropylmethoxypyridin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaaccording to claim
 2. 16. A herbicidal and plant growth inhibitingcomposition which contains at least one substitutedN-arylsulfonyl-N'-triazinylurea of claim 1, together with carriersand/or other adjuvants.
 17. A method of controlling undesired plantgrowth, which comprises applying of an effective amount of a compound ofclaim 1, or of a composition containing such a compound to the plant orthe locus thereof.
 18. A method of inhibiting plant growth, whichcomprises applying of an effective amount of a compound of claim 1, orof a composition containing such a compound to the plant or the locusthereof.
 19. A method of influencing plant growth for increasing yield,which comprises applying of an effective amount of a compound of claim1, or of a composition containing such a compound to the plant or thelocus thereof.
 20. A method of selectively controlling weeds pre- orpostemergence in crops of useful plants, which method comprises applyingof an effective amount of a compound as claimed in claim 17, or of acomposition containing such a compound to the plant or the locusthereof.
 21. A method of inhibiting plant growth beyond the 2-leaf stagepreemergence, which method comprises applying of an effective amount ofa compound as claimed in claim 18, or of a composition containing such acompound to the plant or the locus thereof.